Sodium Hydroxide → HCID 57377415, compound

HRID 1529825Notes

Reaction equation

HRID 1529825 reaction equation
Cl[C:2]1[C:7]2[C:8]3[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=3[Se:10][C:6]=2[N:5]=[CH:4][N:3]=1.[NH2:15][C:16]1[N:17]=[C:18]([S:23][CH3:24])[S:19][C:20]=1[C:21]#[N:22].[OH-].[Na+]>CN(C=O)C>[CH3:24][S:23][C:18]1[S:19][C:20]([C:21]#[N:22])=[C:16]([NH:15][C:2]2[C:7]3[C:8]4[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=4[Se:10][C:6]=3[N:5]=[CH:4][N:3]=2)[N:17]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6764114-Amino-2-(methylsulfanyl)-1,3-thiazole-5-carbonitrileHCID 867005014-Chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene

Product 1

HCID 57377415HCID 57377415, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene (250 mg, 0.917 mmol) in DMF (8 mL) was added sequentially 4-amino-2-methylthio-thiazole-5-carbonitrile (235 mg, 1.376 mmol; Thomae, D.; Perspicace, E.; Hesse, S.; Kirsch, G.; Seek, P. Tetrahedron, 2008, 64, 9309-9314) and powdered NaOH (110 mg, 2.751 mmol) at rt. Work-up as described in example 2, gave the product as a yellow color solid (300 mg, 81%), mp 264-266° C. (decomp). 1H NMR (400 MHz, CDCl3): δ 9.72 (1H, s, H-2), 6.75 (1H, s, exchangeable with D2O, —NH), 3.38 (2H, br s, H-8), 2.98 (2H, br s, H-5), 2.82 (3H, s, —SCH3), 1.91 (4H, br s, H-6,7); LC-MS (positive ion mode): m/z 406, 408 (M+H)+.

Sources & evidence

ORD record
ord-81dd05cd57fd4a02b196783d80fedb69
Source dataset
uspto-grants-2015_07
Patent number
US09090633B2

Reaction notes

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